


Can I get an encore?

by troubleseeker



Category: Supernatural
Genre: Anal Fingering, Anal Plug, Anal Sex, Bottom Jimmy Novak (Supernatural), Coming Untouched, Edgeplay, M/M, Multi, Oral Sex, Public Sex, Rock Star AU, Rock Star Castiel (Supernatural), Rock Star Dean Winchester, Sibling Incest, Spitroasting, Top Castiel (Supernatural), Top Dean Winchester, Top Sam Winchester, Twins, Voyeurism, Winjimstiel, manager Jimmy, needy, roady Sam Winchester
Language: English
Status: Completed
Published: 2019-11-23
Updated: 2019-11-26
Packaged: 2021-02-25 22:08:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,623
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21532726
Author URL: https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker
Summary: Dean and Castiel have made it big as rock stars with Jimmy as their manager and Sam as their roady. They also fuck ... a lot.Sam and Jimmy stand at the very very back of the venue while Dean and Cas are playing to "enjoy the show", and then Sam takes Jimmy back to their green room to wait for Cas and Dean to join their little party. Jimmy can't wait...
Relationships: Castiel/Jimmy Novak/Dean Winchester/Sam Winchester
Comments: 21
Kudos: 53





	1. Chapter 1

**Author's Note:**

> A special thanks to Formidablepassion  for urging me to write this with this ship.  
> And a great big squishy hug to Oddsocksandstuff for giving this a quick beta!

Jimmy looks out across the crowd as the baseline rumbles through the air, never before so glad that no one is looking in  _ his  _ direction. Like, sure, the entire point of being a band’s manager is making damn well sure there was a giant crowd facing the  _ stage _ , but  _ most _ of the time he isn’t getting stuffed full of  _ dick _ .

“Feel so good, Jimmy,” Sam whispers right into his ear, barely audible above the music, and Jimmy shivers; this is so wrong. “Fucking filling you up and no one even knows.” 

_ God it’s also so hot. _

“Gonna get you nice’n ready for them, aren’t I?”

_ Fuck _ .  _ Fuck. Fuck. Yes!  _ Overwhelmed, Jimmy hangs his head, staring at the well-worn venue flooring instead of the brightly lit stage. It’s too much, too good.

“Nuh-uh.” Sam grunts, moving to grab both of Jimmy’s slim wrists in one of his massive paws so he can wrench his manager’s head up by his hair. “Watch em. You like to watch, don’t you?”

Jimmy whimpers, no choice but to stare directly at the stage, and its occupants. And yeah … he’s always liked watching.

“You like watching my big brother sing his heart out,” Jimmy nods, and Sam can feel the tiny little movement, smiles with his teeth around sensitive skin. “Like watching  _ your _ brother too, don’t you?” Sam’s breath is steaming up Jimmy’s ear, tongue already dragging down his arched neck; the giant has an oral fixation. 

Standing there frozen - fully dressed, jeans pushed down in the back only far enough for Sam to have access to his well-used hole - it’s harder for Jimmy to admit to Sam’s last question. And for no damn good reason … Sam’s been a solid part of their poly relationship for years now, has watched Jimmy do terrible things to and for Cas... He’s watched Sam to amazing things to both their brothers … But admitting it still feels dirty.

“Say it.” Sam orders, snapping his hips forward as he drags Jimmy backward. Jimmy groans, pulling in air like a drowning man. God, he’s so full. “Say it! Say you like watching our brothers.”

“Fucking love it.” Spills from his bitten lips, unable to resist Sam … or any one of his boyfriends, really.

“Love what?”

“Love watching our brothers on stage.” He gasps, there’s not a lot of breath to spare when it’s getting pushed out of him in quick grinding snaps. “Fuck. They’re so  _ hot _ .”

“Yeah, they are.” Sam agrees,  _ swiveling _ his hips and Jimmy has to stop himself from moaning. Cas and Dean are good, but the people less than five fucking feet in front of them might recognize the noise as more than just enthusiasm for great music. “And I’m getting you ready for them.”

“Such,” Jimmy curses under his breath, eyes going funny when Sam decides it’s time to ride his prostate. “Such a good roady.” 

“Gonna get you so sloppy, wet, and needy they won’t even need to tell you to ride em, you’re gonna climb up in their laps all by your horny, slutty self.”

Jimmy shivers.  _ Fuck _ . Yeah, he wants that, wants to do a whole lot of things. And if Sam doesn’t let go of his hands till the show’s over … he’ll be frantic enough to climb anyone in search of an orgasm. 

“Keep your head up,” Sam warns, tugging on his hair once before releasing his hold there. 

Jimmy doubts this is going to get easier for him, but he dutifully keeps his eyes glued to the stage; barely aware of which song is playing. Sam’s deft fingers on his right nipple make him go weak at the knees, which pretty much means he’s hanging from Sam’s dick for a full minute. By the time he’s regained  _ some _ of his faculties, the soulful strum of Dean’s guitar signals the show’s first slow song.

A swarm of lighters and mobile phone flashlights light up between them and the stage, and Sam manages to grind  _ exactly _ to the rhythm… Jimmy’s never hearing this song without getting a boner ever again. He’s leaking into his jeans at the thought of what they’re doing … and the thoughts of what they’ll be doing  _ later _ .

By the time Dean croons out the final lyric, audibly impregnating half the audience, Sam loses his rhythm and comes deep inside of Jimmy’s ass. Jimmy can feel him. Feels that massive dick throb as it empties its load inside of him, and the sudden lack of humping means there’s no friction on Jimmy’s dick where it’s still trapped.

He whimpers, shimmying his hips till Sam tightens his hold on Jimmy’s left nipple and he freezes. He shouldn’t have gotten that piercing.

“Don’t move,” Sam warns, releasing Jimmy’s bruised wrists to trap his arms between their bodies instead. Jimmy could probably wriggle his way to freedom but Sam’s lightning-fast; no way would he be free for long enough to undo his jeans, let alone jerk off. He shudders when Sam’s second arm snakes around them both to press tightly against his crotch. The pressure lights him up like a christmas tree, but it’s not enough to get him to come; not without him grinding into that massive palm and he’s not allowed to do that. “Good boy.”

The next song is still rather slow, and Jimmy spends all three minutes and fifteen seconds of it trapped in the most sexually frustrating hug he’s ever been trapped in. Sam’s big enough that even when he starts going soft he stays firmly in place; and its place truly is inside of Jimmy’s ass, perhaps Jimmy’s mouth … or Cas’ mouth… maybe Dean’s perfectly peachy ass. Jimmy shudders at the mental images, no way to alleviate his heightening need. 

When the beat picks up again, the crowd pulsing back to life, Jimmy can also feel every single twitch as the baseball bat gently inflates again just in time for round two.

“You put this set together,” Sam whispers, barely moving as he holds Jimmy close; not that he needs to move very much for Jimmy to feel it … he’s fucking impaled. “How much longer till they finish the encore?”

Jimmy forces himself to pay attention to the song, the lyrics, the lights … fuck.

“Thirty-five minutes.”

Sam hums, twisting Jimmy’s nipple till he feels him vibrate around his cock, suck another bruise right behind Jimmy’s ear.

“Should be able to get two more loads in you before I set you loose backstage.”


	2. Chapter 2

As applause and wolf whistles thunder through the air, Jimmy goes cross-eyed. He has no idea where Sam had been hiding the plug, but truth be told … he doesn’t care.

“There you go.” Sam grins, tongue between his smiling teeth, and pats the thick as fuck toy into place. “All nice ‘n ready.”

He can’t really feel his legs, but he’s not falling over so Jimmy’s happy, trembling with a whole host of emotions as Sam pulls his jeans back up over his ass. He nods at Sam’s questioning, “Aren’t you?” fuck yeah he’s ready. So ready.

“Come on, don’t wanna leave them hanging.”

Jimmy giggles, letting Sam guide him through the halls before they fill with fans who might recognize the both of them. Security raises an eyebrow when he stumbles past them, and he vaguely wonders what they think he’s high on. He smiles at the wall of muscle as Sam flashes his badge and pushes through with ease, and wonders if the front of his jeans are stained with forty minutes worth of precome.

Down a hallway, up some tiny stairs and through a discreet looking door labeled ‘staff only’.

Their green room isn't small, Team Free Will is famous enough now that they play in fancy places with actual lounges with actual leather couches that no one wants to ever go near with a blacklight. Sam shoves him inside and locks the door to the hall behind himself, making sure no sneaky fans are walking in on shit they're not meant to see. 

Jimmy stumbles to a halt somewhere near the center of the room, hands at his side instead of where they want to be. He's so fucking ready to just come, but if he can come with two dicks inside of him he can wait a minute or two. He’s vibrating with tension, eyeing the small concessions table and its diverse contents. Perhaps a snack could calm his nerves? There’s alcohol too, but he’s already so buzzed it might not actually do him any good. 

His mouth feels too empty, what with his ass being so fucking  _ full _ . Just a handful of chips, maybe a lollipop … he sways towards the sugar high, all ready to go distract himself with phallic food and maybe a shot of something after all when thick arms circle around him. 

"Being so patient for us." Sam growls, pinching at Jimmy’s nipples till he’s panting before drawing Jimmy's arms behind his back once more and it makes the need to move so much worse. "nononoooo. Stay still." And then the fucker  _ bites  _ him again because he loves making his boyfriends squirm. The sadist. "We're going to wait right  _ here _ ." Sam licks at the bitemark, nosing into Jimmy's hairline. "And when that door opens, and only then, am I going to let you go. You know what you're going to do when I do that?" 

Mute with arousal, Jimmy whimpers and shakes his head. He hasn’t got a clue what Sam wants him to do, but by God, he’s got plenty of ideas.

“Whoever comes through that door first, you get on your knees and  _ beg _ for their cock.”

Oh holy hell he’s down with that plan. Jimmy sways forward, the strain on his arms increasing as he yearns for someone to walk through the door. He doesn’t give a fuck who it is, as long as it’s Dean or Cas and they brought their dicks. 

“Yeah, you want it don’t you?” Sam eggs him on, holding his wrists in one hand to nudge at the plug hidden underneath his jeans.

Jimmy’s world narrows. There’s the door in front of him, still annoyingly closed, hands around his wrists and pressure in his hole that’s annoyingly static. He bucks back against Sam’s hand just to feel the plug inside of him  _ move _ .

“Such a slut,” Sam says it fondly, they all are. “And you’re all ours.”

How long does it take to get from the stage to their green room? Dean and Cas always stick around to sign some autographs and take some selfies with their die-hard fans, but surely they’ve finished with all that by now? 

“They’re taking their time.” Sam the fucking clairvoyant comments. “Makes you wonder what they’re up to. No one knows you’re waiting for them here, what if they decided to go fuck backstage?”

Jimmy pictures it, and his jeans get that much wetter. Their brothers always get hyped up on stage. High on adrenaline and screaming fans. Dean’s oral fixation could have him on his knees behind one of the speakers; Cas on the lookout while he wastes an orgasm that belongs to  _ Jimmy _ .

“Or maybe there’s too many fans. They can’t disappoint them, can they?” 

The manager in Jimmy, pushed to the side with need need need need, pipes up to say that yes, taking care of the fans is important. But it pales in comparison to how badly Jimmy needs to be taken care of. He growls, bucking back harder to distract himself. God his mouth is empty. He’s about to ask Sam for a couple of fingers -  _ anything _ \- when the giant starts talking again.

“Who do you want to be first?” Sam asks, nonchalant and at ease with three fucking orgasms under his belt. “Dean? Bet he’d fuck your throat all pretty like, just at the sight of you on your knees.”

Jimmy’s dick throbs. Yeah, Dean is a sucker for big blue eyes staring up at him.

“Or maybe you’re hoping it’s Cas? Want big brother to own that mouth?”

Jimmy’s too far gone to throw back his usual reply of ‘he’s only ten minutes older than me!’ and just drools at the thought of Cas palming his cheek and then the back of his head as he slides home. They’ve known each other for all of their lives, and Cas has no qualms in making him deep throat from the get-go; he trained his brother’s gag reflex into non-existence himself after all.

He doesn’t care. Just needs either of them, no, both of them, to walk in and claim him.


	3. Chapter 3

After a fucking eternity, the doorknob turns, and the hold on Jimmy’s wrists disappears. He stumbles forward, then lets himself fall to his knees; already begging.

“Please, please fuck me. Please.”

He knee walks forward, reaching for the crotch at eye level and palming it in desperation.

“Please, please, God, need you to fuck me.”

“Jesus Christ, Jimmy.” 

It’s Dean, and Jimmy turns his baby blues up a notch as he looks up, up, up. No way in hell is Dean saying no when he looks this adorable and sexy as hell … and desperate. 

“Please, Dean. Need your dick, man. Need it. Need it so much, c’mon. Fuck me.”

He’s tearing at buttons and zippers and belts, hands unhindered for the first time in  _ hours _ , and fuck it’s good. Jimmy yanks down boxer briefs and stuffs his head against stage light warm skin. Mouths at the coarse hair and sweat, down to the one thing he needs right now. 

Dean curses up a storm, hands finding purchase in Jimmy’s hair as he tries to stop himself from just keeling over. 

Jimmy licks his way down, finds soft, sensitive skin and kisses and suckles at it till Dean’s dick springs forward in all its glory. 

“Can I suck you?” He begs, eyes locked on Dean as he does his best to not just eat the other man alive. “Please, De. Please, want you. Please. Plea-”

His begging is interrupted quite suddenly by Dean grabbing his head, holding his mouth open with a thumb, and shoving his dick into it. Jimmy gurgles happily, eyes rolling back as Dean sets a soothing rhythm.

“What the fuck did you do, Sammy?”

“Just got him ready for you.” Sam answers non-committedly, settling down to watch as Cas finally manages to shoulder his way past the Dean shaped roadblock and close the door. 

“You been waiting for us back here all this time?” Dean coos, frowning when Jimmy sucks him deep and shakes his head no.

“You watch us from backstage?” Cas asks, crouching down next to his twin to haul his hips back and unbutton his jeans.

“Nope.” Sam, sounds  _ very _ smug. “Snuck to the back of the venue and fucked him through the show.” 

“You were in the  _ crowd _ ?” Dean sounds impressed.

“Yup.” 

“Fuck that’s hot.”

“Slicked him right on up for you.”

Jimmy gags himself on Dean on purpose, demanding more attention. Sure, Sam fucked someone at the back of a crowd, but  _ he _ let himself get fucked at the back of a crowd.

“Fuck. Yeah, baby. You did good too. Everyone looking at us when they had a real show going on right behind em.”

Cas drags Jimmy’s jeans down, all the way down this time, and Jimmy’s this close to crying out in relief that his dick’s finally out in the wild. His brother gives him a single tug before concentrating on his already well-used hole. 

“Shush.” Cas tells him when he whines at the injustice and spanks him a couple of times just to make sure he knows who’s in charge. “You waited this long you can wait some more.”

“There’s three loads in there.” Sam offers, and then there’s the telltale sound of a beer bottle opening. 

“You came three times and made him wait?” 

“Mhmm.”

It’s harder to concentrate with Dean’s dick down his throat, but Jimmy is dimly aware of plans brewing that he might not be thrilled about in the short run.

“How many you wanna put in him before you let him come?”

It takes Jimmy a while to realize exactly what they’re talking about, and his hindbrain riots. He’s been waiting for this for hours already. He earned his right to come hanging off Sam’s dick in a very public space. But when he tries to pull off of Dean’s dick to give them all a piece of his mind, Cas shoves him right back down. 

Having a dick forced down his throat is strangely soothing, and Jimmy relaxes into his brother's control. Fingers pressing and then pulling at his plug push him that bit deeper, and he feels that mental shrug as he passes into acceptance. 

“Such a good boy.” Cas tells him, scratching soothingly even as he holds Jimmy in a full deep-throat. “Don’t worry, we’ll take care of you.”

He hums, anoxia settling in around the edges of his consciousness as he’s kept in place. 

“Fill your greedy hole right up.”

Dean rocks into Jimmy, tiny little thrusts never taking him far enough for him to breathe, but enough to settle into the rhythm. When Dean finally lets him move back far enough to breathe, Cas pulls out the plug with a dire warning.

“Arch that back, don’t wanna waste any of Sam’s come, do you?”

Jimmy clenches, pulling in breaths as he sucks Dean down. It’s an energetic blowjob, messy and full of every trick Dean lets him get away with.

“Fuck, gonna come.”

“Do it.” Cas hisses, shoving three fingers into Jimmy’s hole so his glassy eyes fly wide open to stare unseeing at Dean’s O-face. He’s so loose and wet, there’s barely any resistance. Dean grinds home, fingers curling painfully tight in Jimmy’s hair as he loses it. 

After three loads in his ass, it’s a welcome change of scenery. Jimmy rolls his eyes back and slowly lets the pressure off of Dean’s dick. 

“Thank you.” He moans, making a show of licking Dean’s dick nice and clean before planting a sweet little kiss on the rosy head. Dean laughs, shoving his head away to shuffle to the fridge with his jeans still halfway down his legs. Jimmy looks over his shoulder, squeezing around his twin’s fingers as he raises his eyebrows in challenge. “You gonna let me come now?”

“You’re a brat, you know that?” Cas grins, shoving his fingers deep before pulling them all the way out. “Lose one drop of come and you’re waiting till our next gig.”

It’s not an idle threat, and Jimmy knows it. 

“That’s in three days!”

“Better keep that hole nice and tight then!” Sam calls across the room. Way too happy about keeping Jimmy hopped up on pure hornyness for days at a time.

“What Sam said.”

Jimmy whimpers, lowering his torso to the floor to make failure less likely. He’s not above a bit of groveling - not against a bit of edging either, but he’s in more of an I want to come  _ now _ mood. He watches Cas saunter over to the couch and plop his amazing ass down next to Sam’s giant sprawled form. Jimmy’s pretty sure where this is headed, eyes caught firmly on his brother’s hands.

And yeah, he’s getting his dick out. An identical specimen to Jimmy’s own frantic member; they checked very thoroughly.

“Come on, Jimmy.” Cas calls, eyes dark and full of promise as he pats his lap. “You wanna come you’ll have to earn it.”

Jimmy has two options. One, crawl ass up to his twin’s call and ride him like he’s never been ridden before. Or two, speed wank and  _ then _ ride his brother as he apologizes. 


	4. Chapter 4

**Notes for the Chapter:**

> the last chapter!! Hope you've enjoyed the ride, thanks for getting through this with me!

“You fucker! Dean, hold his hands.”

Jimmy curses, hunching over to try and keep his hold on his dick in the small space between his and Cas’ stomachs. He’s pretty sure Castiel somehow managed to leach all of the patience meant for the both of them into his own thick skull while still in utero. The bastard is too fucking hard to rile up, and  _ he’s  _ too impatient for his own good.

“Nooo.” He begs pathetically, squirming where he’s impaled on his brother’s dick, and failing to keep his hands out of Dean’s grasp. “I’m sorry. I’ll be good.” 

No man, living or dead, should be able to resist him once he’s crawled up into their lap like a sexy … something. He’s pretty sure he saw Sam’s dick twitch inside of his jeans where he’s still lazily lounging, and Dean made a hungry noise, so he  _ was _ sexy. Somehow, Cas was completely unfazed and realized where his hands were going even after he got his dick wet.

“I wasn't going to come. I swear. Just wanted- I needed it, man. Please.”

Dean pulls his arms back, and Jimmy’s dick hangs ignored once more. It’s a tragedy, and one Jimmy intends to get payback for at some point.

“You don’t need to hold me, I’ll be good.” He promises. It’s a lie; his hands are itching to get right back to jerking off.

“Sure you will be.” Dean laughs, gathering Jimmy’s hands together nice and neat where Castiel wants them.

“I could have jerked off before I rode him!” Jimmy argues, as if that made up for his wandering hands. And right now he regrets the decision to be obedient just a bit.

“Mhmm.”

“I wasn’t even going to-ah- wasn’t going to come yet! Fuck, Cas- right there. Oh my god.”

“Put some effort into this,” Cas slaps Jimmy’s thighs, spread wide around his waist. “letting me do all the work here. I could get a better fuck off of one of the fans in the hallway.”

“You wouldn’t  _ dare _ .” Jimmy hisses but tilts his hips along with his brother’s movements till he gets the rhythm going. 

“Wouldn’t I?” Cas laughs, a devilish glint in his eyes. “I’m a rockstar, Jimmy. Throngs of fans who’d kill to be in your place.”

“They’d never be enough.” Jimmy swivels his hips, leaning back into Dean’s hold to put more effort into his moves. “None of them know what you need.”

Castiel’s fingers dig into highs, urging him to keep going.

“You do, don’t you? You know what I need.”

“Fuck- fuck yeah.” Jimmy’s dick bounces up, smacks wetly against his belly; he whimpers.

“Then give it to me.”

Jimmy moans, unable to resist that voice, those eyes … that dick. And rides Cas like he knows his brother loves. Clenches his hole tight on every upstroke, and sticks to the rhythm like a drummer till he’s breathing like he’s running. 

Cas takes over when he gets close, hands migrating to Jimmy’s hips and moving him as he wishes, harder, faster, deeper, and then holding him completely still while he adds his own load to Sam’s three.

The eternal cuddler, Castiel then pulls him close. Jimmy rests his head on his twin’s shoulder, breathing hard and trying (and failing) to ignore his own raging erection. Dean’s still holding his arms captive.

“Is this the right time to ask about me  _ finally _ getting to come?” He hedges, but groans at Cas’ chuckle. 

“How many did Sam get in you again?”

“Three… C'mon, Cas. Please?”

“I think me ‘n Dean should get two each first.”

Jimmy squirms, earning a sluggish spank to the rump as he overstimulates Cas’ softening dick. “C’mon, man. You can still fuck me after I come.”

“Oh we’re planning to.” Dean rumbles, and the picture that paints makes Cas swat at him again; too hot.

“Don’t wanna wait, Dean. Wanna come now. Please let me?” Dean’s a sucker for begging, so Jimmy puppy-eyes him over his shoulder. “Need it. I’ll be so fucking good. Promise. Just wanna come, man. Waited so long, been so patient. Let Sam fuck me the whole show, and he teased me too.”

Sam makes assenting noises, and struggles into a sitting position so he can kiss first Jimmy and then Dean. “Fuck yeah, I did.”

“Waited so long, Dean. Please.”

“Turn him around.” Dean orders, releasing Jimmy’s hands and grabbing his shoulders instead. “Fuck off, koala bear. You can still cuddle him if he’s turned around.”

A bit of shuffling and plenty of overstimulated whimpers later, Jimmy is facing outward. Still planted firmly on Cas’ half-hard dick and still very hard himself. He’s kept his baby blues set to ‘pretty please’ and his hands to himself, so really he’s earned this orgasm. Best boy, Jimmy. Golden star and a couple of sparkly stickers.

Cas pulls him close in another crushing hug; effectively trapping Jimmy’s hands once more … just in case he gets naughty ideas. When Dean shucks his jeans and brandishes his newly revived dick at him, Jimmy cottons on to their plan. His mouth starts watering instantly. 

“Yeah. C’mon.” He urges his boyfriend on, leaning forward like he’s drawn to Dean’s dick like a sexy magnet. “Give it to me. Fill me up, Dean. Need you to.”

“Such a hungry boy.” Dean coos. Jimmy doesn’t try to correct him. It’s true. They love it. “And such a good boy too.”

Castiel lets him lean forward, watches over Jimmy’s shoulder as he sticks out his tongue and reaches as far as he can.

“Letting us take care of you even when you really want to tell us to fuck off.”

At the end of his reach, already fucking himself on Cas’ cock to try and maintain his balance, all Jimmy can do is lap at the wet head of Dean’s dick. 

“Fuck, so good.” Sam whispers, reaching over to slide two fingers into Jimmy’s straining mouth; press down on his tongue. “Don’t be a tease, De. Get in there.”

“How dare you call  _ me _ a tease,” Dean scoffs, but he finally inches close enough to feed Jimmy his dick again.

Sam slides his fingers out again, smearing spit down Jimmy’s chin as he palms their boy’s neck. “Go deeper, wanna feel you.”

“Bossy.” 

“Just do it, jerk.”

“Bitch!”

Jimmy gags once, breathes through his nose, and then opens his throat to let Dean do as Sam asked. It’s an intense feeling, being choked inside and out; makes him feel even more full than he already is. 

He gurgles happily when Cas’ dick perks up again. So full. So fucking full. It’s perfect.

It takes all of them a minute or two to find their rhythm, but eventually, they’re all rocking in and out of Jimmy’s lax body in tandem. Jimmy breathes, hangs from their combined grasp and lets the sensation roll over him. Rides waves of pleasure until he can feel his own orgasm build without any helping hands. 

Turns out, sitting on Cas’ dick and leaning forward makes it very hard for Cas to miss his prostate.

“Fucking hell.” Sam breathes, leaning away to check out the mess dripping from Jimmy’s cock onto the floor. Watching with rapt attention as their happy little toy comes hands-free at long last.

Jimmy barely hangs on to consciousness, pleasure so long withheld wreaking havoc in his brain as Dean and Cas both continue to fuck him. He’s so full, yet so loose and ecstatic. Every pass of Cas’ dick sends new jolts of almost too much pleasure into his system, and Dean seems intent on making sure he’s as deep inside Jimmy’s throat as he can possibly get.

He doesn’t pass out, just … checks out for a bit. Lets himself float on what they give him, feels the pulse of two more orgasms fill him up before he’s hoisted up and draped over the couch. 

“Did so good for us, Jimmy.” Dean praises, peppering him with kisses as Jimmy lifts a wobbly hand to give them a thumbs up. 

“Only two more to go.” 

**Author's Note:**

> If you want to come yell at me on [tumblr](http://ryugarika.tumblr.com/) ... feel free to, I can take it.
> 
> Comments feed me!


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